While there’s no shortage of adventure to be found on a Caribbean vacation, sometimes, the best activity is none at all. Kick back with a tropical cocktail at one of these six incredible Caribbean beach bars, where you can admire the ocean blues, enjoy refreshing island fare, and maybe even plant your feet in the sand. If wanderlust strikes, a Caribbean escape is only a Tradewind flight away.
Cip by Cipriani’s, Anguilla
Photo: Cipriani Anguilla
Anguilla resort Cap Juluca reopened in December 2018 as a new flagship Belmond property, and its reincarnation brought in a slew of incredible beachfront bars and restaurants. Our favorite: Cip by Cipriani’s, an offshoot of the Belmond Hotel Cipriani’s culinary hotspot in Venice. Grab a front row seat by the impossibly beautiful Maundays Bay, order a bottle of rosé and some classic Italian bites, and let the hours slip by.
Eden Rock Beach Bar, St. Barths
Photo: Laurent Benoit
Eden Rock St Barths’ fabulous beach bar is up and running — and buzzing. St. Barths’ legendary people watching, celebrity spying, and fashion spotting comes to life across St. Jean Bay, with a cold glass of fine French wine in hand. Enjoy the views on a high-top stool at the bar, or get cozy on a beach lounger.
Plage, St. Barths
Photo: Plage via Le Sereno
In rebuilding Le Sereno St. Barth after Hurricane Irma, the property added a new toes-in-the-sand beachfront restaurant, Plage. With prime views of Grand Cul de Sac bay, it has the kind of vibe that makes you want to stay a while. As the palm trees sway above, sip on a Sereno Spritz (June liqueur, freshly muddled raspberry, grapefruit juice, peach bitters, and prosecco), nibble on the red Sicilian prawn carpaccio, and take in every moment of the good life.
Sandy Island, Anguilla
Photo: Paul Rubio
When Hurricane Irma struck in 2017, she swallowed much of Sandy Island, which was home to an eponymous beach shack. But Sandy Island has resurfaced with a dreamy 360-degree beach, a rebuilt restaurant pavilion, and plenty of umbrella-capped beach beds for those languid beach days. Order the “Crazy for Crayfish” — it’s the Anguillan delicacy in its best BBQ form — and wash it down with the secret-recipe JoJo Rum Punch. You can access this slice of paradise by private boat or the island’s daily water shuttle, which leaves from Sandy Ground Beach on the Anguilla mainland. Oh, and prepare for a wet landing (it’s part of the experience).
Soggy Dollar, Jost Van Dyke, BVIs
Photo: Soggy Dollar Bar
No beach-bar hopping experience across the British Virgin Islands is complete without a stop at Soggy Dollar, a Jost Van Dyke icon. After all, this is where the “Painkiller” cocktail was born and perfected in the 1970s. Following a 2018 rebuild, it’s once again possible to enjoy this heady mix of premium dark rum, cream of coconut, pineapple, and orange juice (topped with fresh-grated Grenadian nutmeg) with local yachters.
Sunshine’s Beach Bar & Grill, Nevis
Photo: Four Seasons Resort Nevis
Though it’s situated right next to the gorgeous Four Seasons Resort Nevis, there’s nothing glamorous about Sunshine’s Beach Bar — and that’s exactly its charm. The brightly colored bar is low on frills and packed with local barflies, and it pumps out reggae music day and night while serving super-strong drinks that’ll knock you off your feet. For the true Sunshine’s experience, order the “Killer Bee” rum punch, which goes down way too easy and, as the name suggests, stings in the end. Sunshine’s is the kind of under-the-radar bar you’ll reminisce about long after your Caribbean vacation (at least, what you can recall).
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Tradewind Aviation offers regularly scheduled service to St. Barths and Anguilla, and private charter service to Nevis and the British Virgin Islands.